200636-15-3

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3S)-1,4-dibenzyloxy-3-(3-hydroxypropoxy)butan-2-ol is used as a potential pharmaceutical candidate for various applications due to its structural complexity and potential biological activity.
Used in Chemical Industry:
(2R,3S)-1,4-dibenzyloxy-3-(3-hydroxypropoxy)butan-2-ol is used as a complex chemical compound in the chemical industry for various applications, taking advantage of its multiple functional groups and stereochemistry.

Upstream product

• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 
• 504-63-2 trimethyleneglycol 
• 80183-15-9 (2R,3R)-1,4-bis(benzyloxy)-2,3-epoxy butane 

Downstream Products

• 1101134-01-3 (4R,5R)-5-(benzyloxymethyl)-12,12-dimethyl-1,11,11-triphenyl-2,6,10-trioxa-11-silatridecan-4-ol 
• 239100-37-9 (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene 
• 239100-36-8 (5Z,7E)-(1R,2R,3R,24S)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene 
• 200636-22-2 (2R,3S)-1,4-dibenzyloxy-3-(3-pivaloyloxypropoxy)butan-2-ol 

Relevant academic research and scientific papers

Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity

2α-and 2α-Substituted analogs of 14-epi-previtamin D3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D3 triene at 80 °C.The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2a-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D 3.We found that modification at the C2 position of the seco-steroidal skeleton afforded interesting effects for biological genomic activity for the pre-vitamin D form as well as the natural vitamin D form.

Synthesis of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]

A convergent synthesis of biologically interesting 20-epi-eldecalcitol which possesses an inverted C-21 methyl substituent at the 20-position of the side chain of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (eldecalcitol) is described.

Two convergent approaches to the synthesis of 1,25-dihydroxy 2-(3-hydroxypropoxy)vitamin D3 (ED-71) by the lythgoe and thf trost coupling reactions

Two convergent syntheses of 1,25-dihydroxy-2-(3-hydroxypropoxy)vitamin D3 (ED-71) by the Lythgoe coupling reaction between the A-ring phosphine oxide and the C/D-ring ketone and the Trost coupling reaction between the A-ring ene-yne and the C/D-ring bromomethylene are described.

Synthesis and biological characterization of 1α,24,25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (24-hydroxylated ED-71)

24-Hydroxylated derivatives were synthesized in 24(R) and 24(S) forms by the convergent method as analogs related to 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3. In the convergent synthesis, the A-ring fragment, synthesized from diethyl D-tartarate, and the C/D-ring fragments in 24(R) and 24(S) forms (vitamin D numbering), obtained from vitamin D2 via the Inhoffen-Lythgoe diol, were coupled in moderate yields to give 1α,24(R),25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3 and 1α,24(S),25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3. In preliminary biological evaluations, 24-hydroxylation of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 caused weakened affinity to vitamin D binding protein in vitro and less calcemic activity in vivo compared to the parent compound. While the affinity to vitamin D receptor in 24(R) epimer was sustained, the affinity in 24(S) epimer was less than that of the parent compound. Copyright

Convergent synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

A convergent and versatile synthesis of the potent vitamin D analog, 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 [1] (ED-71) is described.